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Harmaline fb reduction to THH, condensed thread

tregar

tregar

Rising Star
Trips here at the forum posted:
Hey all. A very close friend of mine asked me to report on a 'presumed' successful THH "synthesis". (Simple reduction) There were some bumps along the way, but it all worked out well. This is awful laboratory technique.

Used many peganum harmala seeds, salted out ala Manske, then performed an A/B on the Manske Product.

The resulting 4.8 g tannish powder was dissolved in enough 10% HCl to completely dissolve it and put on a hot plate with a reflux condenser. The mix was brought to a boil. Zinc powder was slowly added to the round bottom flask, and given time to boil and fizzle before more was added. Zinc continued to be added over the course of an hour until fizzing stopped. ~50 mL 10% HCl was added and more zinc was slowly added. Anytime one of the reagents was clearly expended, more of it was added (very scientific of him, eh?). Eventually, the dark red colour of the mix turned yellow, then clear with just the faintest hint of pale baby yellow. This was left to continue fizzing away for an hour or so.

When it became obvious that the compound was not getting any lighter in colour, a few scoops NH4Cl was added and the whole mix was filtered through celite (...you don't have celite and a fritted funnel? Then a coffee filter lol) and the alkaloids were extracted with six additions of ~75 mL Ethyl acetate. The ethyl acetate was rotovapped. (What, you don't have a rotovap? Food Dehydrator'ed then.... lol). Dirty brown goo was left behind. 10% HCl was added and this was shaken (awful technique) this resulted in a disgusting coloured nasty chunky liquid. This was rotovapped. To aid the the drying process, blasts of DCM were added to the round bottom periodically and shaken.

This refused to dry (due to the awful technique of acidifying with aqueous) and so the brown glob had ~75 mls of ethyl acetate and 75 mls DCM added. It was shaken vigorously. Everything but the good stuff went into solution leaving brown liquid and white crystals. These were filtered and washed with DCM. These crystals were taken up in 150 mLs of isopropanol/methanol in a 50:50 ratio. This was refluxed and once it began boiling, water was slowly added dropwise and given time to resume boiling until everything was dissolved and the solution was clear. The hotplate was turned off and almost immediately, beautiful fractally snowflake crystals began to form. The flask was allowed to cool to room temp and then put in the freezer. 150 mls of isopropanol were also put in the freezer.

When everything was cold, the crystals of the flask were filtered out and washed with the cold iso. Beautiful shimmering perfectly white crystals resulted. These were weighed and found to have a mass of ~3.5 grams. Thin Layer Chromatography revealed that the compound was indeed distinct from either harmine or harmaline. No NMR was run. Bioassay revealed good times and despite the huge amounts of coffee my friend had been drinking, no hypertension was noted, which most definitely would not be the case had it been harmine/harmaline.

A much more effective and much faster technique involved taking the ethyl acetate fractions and adding methanolic Hcl (made from methanol + acetyl chloride). The compound fell out of solution immediately, in similar yield and was filtered and recrystallized as outlined above.
Click to expand...
This works.
 
A bit of reaction solution is taken up on q-tip and rubbed onto a paper plate and held under a 4' long blacklight, it gives off a light blue glow under UV light (right) while original harmaline glows yellow-green.
 
For what it's worth, here is the ending result, a few drops of water is dabbed on a q-tip and smeared in the THH, and rubbed on a paper plate, here it is on the right, to the left is the starting harmaline that was used. The harmaline glows green-yellow, while the THH glows light blue.
 
After meditating on this for 4 hours and noticing a peculiar trait in the process each time, perhaps figured out how to seperate the zinc carbonate from the THH without even having to use everclear or any additional chemicals. But don't know if it will work yet in practice.
 
Let me make sure it works in real world practice in a few days before explaining. Long work schedule ahead before day off. Good idea though Auxin, on right track.
 
Wondering if the thh can be mansked.
Somewhere ron69 mentioned it does but it took a long time he said, much more than harmine/harmaline.
 
Yes Jees, it should work, suppose you have only crude THH crash out to the bottom of your filtrate, then after decanting the top alkaline layer, take the bottom alkaloids up in new hot vinegar and perform a Manske on it. This would be a great way to clean up your THH and purify it further.
 
Have some problems to work out still on the conversion, it's low yielding, less than 40%.
 
Good work brother :)

Thanks for sharing, and the pics! I'd love to do some more experiments with this and analyse it after... but it's gonna have to wait a few months, maybe early next year I can start doing this again.

What was the yield with the manske precipitation? BTW I recommend redissolving the manske precipitation and base-precipitating it afterwards since the manske precipitation might have some salt impurities which could make the final weight a bit misleading.

Oh and, if the final yield isn't very high, don't worry about it.. It's obviously nice to try to make it as efficient as possible but sometimes chemistry practice isn't as easy as the theory, it's normal to have yield loss... Either way this is good stuff :)

Be well!
 
Hi Brother Endlessness.:d I even remember Brother Auxin posting in your original thread, and welcome Brother Jees. Thanks for the kind words.
 
I had a question about the amount of harmine and THH and dmt I use, personally & subjectively I found that for my body weight, 150mg of harmine freebase will strongly activate an amount of dmt in the range of 20 to 35mg, so that's what I use along with the same amount of THH (150mg) or more. Jonathan Ott found 120mg of harmine freebase dosage (not the hcl) to activate 35mg of dmt, while 160mg activated it really strong for him, this is discussed on page 250 of "Pharmacotheon" the hard to find all time classic book, I found what works for him, also works for me, thankfully. I don't use more harmine than this, because it is not needed, it only makes me nauseous if I use much more harmine than this. The THH imho adds intense color saturation effects to the visions and visuals, ie neon colored visions and geometrics, it also shifts the journey away from the mushroom region into the frequency dominated more by LSD, with great energy, clarity, focus, euphoria, and cosmic expansion, ooohing and ahhhhing is something I do alot of with the added THH, it is simply heavenly, and music sounds supernatural and very beautiful with all 3 chemicals.

The vibrational energy that can be felt throughout the body with the addition of THH is much higher than without it, it also helps to eliminate or reduce "confusion", and when it does strike, it is decidely more "acid-like". This increased concentration and focus is necessary as taking Ayahuasca is like entering into a "school" just as Shanon describes it, with a theme & lesson to each journey, however, the most important effect of the added THH imho is that it makes "Real Ayahuasca" style visions possible, just like those painted by Pablo Amaringo, see here. None of the visions repeat according to Benny Shanon, I only can relate these subjective differences between journeys that have the added THH, as I myself, conducted 7 experiments in the past over a course of several months, in these journeys, I took harmine + dmt only, and then the following week took harmine + THH + dmt together, and noted the differences in my journal at that time. Visions like those by Amaringo are made possible as illustrated here, I have seen these kinds of brightly lit and very colorful images with closed eyes with the addition of the THH, however without the THH, I do not see these kinds of images, which at first illustrate this world, and them much later, Ayahuasca shows you other worlds. With eyes open a new reality is revealed as well, the new world looks quite beautiful and enchanting & Sacred, like on mescaline. The Divine is reflected in all of creation. Strange, but my Grandmother was an oil painter, and one of her mystical style paintings was similar to one of his, where the lost city of Atlantis was illustrated.

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Thanks DreaMTripper. 99.9% ammonium chloride from the livestock store in the animal medical isle, 2lbs for $7, the pretty cow girl found it for me. THH xtals are much finer and tinier than harmine or harmaline xtals, they almost require that you use a very heavy vacuum to suck the solution thru a fine micron filter to catch all of them. They like to hang in suspension, though they do work their way to the bottom of the solution jar over much time in fridge, but why wait, just vacuum them off. No smell after dry, needs manske to clean it up, very active. However, plan to do Manske on the rest to get it ultra, ultra pure, and convert to the hcl. Also, A 25mg sample dissolved instantly into 95% ethanol, and stains light blue under UV light. You need to always change the oil in your vacuum pump after each use to keep your pump in top condition. Is there a black hole in the universe where all the stir bars disappear to? 😁 I've lost all my stir bars but one over 4 weeks.

Please take note: earlier in the day, I performed a co-precipition prevention test step. What I did was run the reduction noted above in steps 1-9 (200ml vinegar + 8g grey zinc metal dust spun for 3hr at high speed) without adding 2g of harmaline fb. I ran it for 3 hours, then I prepared a mid-saturated solution of 473ml (2 cups) of hot water with 60g of sodium carbonate, allowed to cool to room temp, then added all of this slowly to the very pale yellow filtrate, I observed 0% zinc metal salt fallout. Ph was measured and found to be ph=9 of solution. This proved (to me only) that 30g of ammonium chloride prevented metal salt precipitation. What happens each and every time without the addition of ammonium chloride, is that you end up precipitating out a thick layer of zinc carbonate which immediately falls straight to the bottom of solution when you add mid-saturated sodium carbonate solution. Anyone can run this test, which is by all means a requisite before performing the actual redution, to prove that when the procedure is done corretly, only THH crashes out. I will be performing a melting test on the THH next week, I don't have time curently. In one of my test the previous day, I determined that 6g of ammonium chloride was insufficient to stop the precipitation of a solution of 3g zinc carbonate salts pre-dissolved into a solution of vinegar, so that's why I raised it to 30g. I stress that this whole procedure including the pre-testing is advanced and not for beginners, it took a month of research and work to arrive at this conclusion.
 
So.... I had a very strange re action occur with the thh reduction method. I have done this method a few times before and what i'm about to explain has never happened before. So I had some relatively pure Harmaline. I'm guessing around 80-90% pure, probably around 5 grams or so that I got from a rue extract and separation. I sometimes don't mind a bit of harmine impurity in my thh, and because I don't have an accurate ph meter it is very difficult and a long process to get pure Harmaline..

So I did everything as I normally do (and others here as well). I used the same zinc powder that I have used in the past. The vinegar is from a different source though, but has shown no signs of causing any problems or containing any impurities.

So basically, I did my thh conversion. And did another acid/base to remove any excess zinc that might be there. Then did about 15 washes with water to clean it. The water was still a bit yellowish looking even on the 15th wash, but I decided since I had done so many, it was as clean as it was going to get. So I poured the water solution containing freebase thh (presumably) and harmine through a coffee filter. I collected the powder and then went to let it dry. I put it on a glass baking tray which was tilted at an angle so any excess water could run off. A little excess water pooled at a low spot at the bottom. I left the tray for a couple of days in the closet to let the powder dry.

Btw, the powder was slightly off white due to harmine impurities. The powder had stayed the same color for many days during the washes and drying. I never noticed any change. Here's where it get's interesting. So I noticed that where there was that tiny pool of water at the low point on the tray, there was a left a small residue of dark reddish purple powder. I thought that was odd but did not think too much of it at the time.

So I proceeded to put my thh/harmine powder in a bag since it had dried completely and stored it with my other goodies in a box. A couple of days after I did that, I went back to the goodies box, looking for something else, and I noticed a bag with bright pink powder in it....I was like...wtf is that....well it turns out that it was my thh/harmine mix.....So i proceeded to do another acid base to see if I could remove whatever impurity had contaminated it....well I did an acid base, and the powder is deep dark purplish red...It is a truely beautiful color, but obviously not what I want. I am considering trying a manske on it, but to be honest, i'm not sure that I would want to consume it, even if I was able to make it white again. I did a tiny taste test, just to see.....but it had no taste...I must have tried about .5 mg though..or less...

So any chem experts care to offer an explanation of what happened?.....Wondering if it could be something alchemical?

On a side note, years and years ago I did a rue extraction and had a jar of liquid with harmine and harmaline in it...It was a deep reddish brown, extra saturated solution....I was in the process of basing it with sodium carb (or bi carb..cant remember) and I added some base and poof, all the liquid went perfectly clear. (nothing had precipitated at this point) I thought...wow...wild...what just happened? I proceeded to add more base and everything that came out was nearly pure white xtals. They were very potent. So i dunno what is going on. I've probably done 20 rue xtractions and 5 or 6 thh conversions, so I generally know what i'm doing...Sorry bout the long rant. Hope someone's got some ideas:?
 
Hi arcologist, I remember you from the original thread, great work back then. Synkromystic, did you at any time in your acid/base or any other time in your process use naoh? I only ask because way back 4 weeks ago when I was trying a failed sodium zincate experiment with excess naoh to ph=13, that I believe the excessive naoh "could" have been detrimental to the THH molecule, I noticed a bit of it would stain "red" when I rubbed some into my skin by accident, held it under blacklight, and I could see the red staining color, I stayed away from high ph solutions after that experiment. Have not seen the red since avoiding naoh. The material really starts to shine at around the 200mg level, quite a bit of sparkle and color intensification with sense of well-being & increased focus. Taken 250mg today, and it's just like it is supposed to be, after this will take a 1 month break before using it again, There is a moderate tolerance noted that lasts up to a week, best if used only once or twice a month in dreams. Definately do a Manske on the material, and any additional steps, then to the hcl. It seems to peak some 5 hours later, as the half-life is 11 hours.The effects from the 4rth hour on, are nice. This has proven to even be a difficult task for me, as the original paper gives zero specific amounts of any of the chemicals to use, that's just plain bad science. For an easy method, Just give Professor8's method a try which involves boiling and vitmain C, at the beginning of this thread.
 
As a matter of fact, I've had it with the whole zinc metal co-precipitation thing, it really is arduous and crazy, what a headache.

thanks Snozzleberry.:)

Forget the seiddei (or however you spell it) original paper with zero amounts of anything to use from 1983. It's like the "Call me, Maybe!" song, Either you call me or you don't. I know to admit when I'm wrong.
 
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